Herbicidal substituted 3-aryl-pyrazoles

Abstract

The invention herein relates to certain substituted-arylpyrazole compounds, herbicidal compositions containing same, herbicidal methods of use and processes for preparing said compounds.

We claim: 
     
       1. A compound according to Formula I: ##STR13## and agriculturally acceptable salts and hydrates thereof wherein R 1  is independently C 1-8  alkyl; C 3-8  cycloalkyl, cycloalkenyl, cycloalkylalkyl, or cycloalkylalkyl; C 2-8  alkenyl or alkynyl; benzyl; or said R 1  members substituted with halogen, amino, nitro, cyano, hydroxy, C 1-8  alkoxy, C 1-8  alkylthio, --C(═X)YR 8 , --C(═X)R 9 , YR 10 , or NR 11  R 12  ; R 2  is C 1-6  haloalkyl;   R 3  is C 1-6  alkyl, C 1-6  haloalkyl, CHO or CH 2  OH;   R 4  members are independently an R 1  member, C 1-8  thioalkyl, C 1-8  polyalkoxyalkyl, carbamyl, halogen, amino, nitro, cyano, hydroxy, C 6-2  aryl, aralkyl or alkaryl, --C(X)YR 13 , --C(X)R 14 , YR 15 , or NR 16  R 17  group; or two R 4  groups may be combined through a saturated and/or unsaturated carbon, or --(C═X)--, linkage to form a cyclic ring having up to 9 ring members which may be substituted with an R 1  member, halogen, amino, nitro, cyano, hydroxy, C 6-12  aryl, aralkyl, alkaryl, --C(═X)YR 13 , --C(═X)R 14 , YR 15  or NR 16  R 17  ;   X is O, S(O) m , NR 19  or CR 20  R 21  ;   Y is O, S(O) m  or NR 22  ; wherein at least one R 4  member is a non-halogen;   R 8-22  are hydrogen, C 1-8  alkyl, C 3-8  cycloalkyl, cycloalkenyl, cycloalkylalkyl, or cycloalkylalkyl, C 2-8  alkenyl or alkynyl, benzyl, or said R 1  members substituted with halogen, amino, nitro, cyano, hydroxy, C 1-8  alkoxy, C 1-8  alkylthio, C 6-2  aryl, aralkyl, alkaryl, carboxyl, alkoxy C 1-8  -alkyl, C 1-8  alkylamino, di-C 1-8  -alkylamino, C 1-8  alkoxy, or carbamyl;   m is 0-2 and   n is 1-5.   
     
     
       2. A compounds according to claim 1 having formula ##STR14## and agriculturally-acceptable salts and hydrates thereof wherein R 1  is C 1-6  alkyl; R 2  is C 1-6  haloalkyl;   R 3  is C 1-   6  alkyl, C 1-6  haloalkyl, CHO or CH 2  OH;   R 5  and R 6  are independently halogen; and   R 7  is an R 1  member, ##STR15##  YR 10 , or NR 11  R 12 .   
     
     
       3. A compound, salt and hydrate according to claim 2 wherein R 1  is CH 3  ;   R 2  is CF 3  ;   R 3  is CH 3 , CH 2  F or CF 2  H;   R 5  is F;   R 6  is Cl; and   R 7  is ##STR16##   
     
     
       4. A compound according to claim 3 wherein said compounds are selected from the group consisting of 2-chloro-5-[1,4-dimethyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-4-fluorobenzoic acid, 1-methylethyl ester;   2-chloro-5-[1,4-dimethyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-4-fluorobenzoic acid ethyl ester;   2-chloro-5-[4-difluoromethyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-4-fluorobenzoic acid, 1-methylethyl ester; and   2-chloro-4-fluoro-5-[4-(fluoromethyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]benzoic acid, 1-methylethyl ester.   
     
     
       5. Herbicidal composition comprising an adjuvant and a herbicidally-effective amount of a compound according to Formula I: ##STR17## and agriculturally acceptable salts and hydrates thereof wherein R 1  is independently C 1-8  alkyl; C 3-8  cycloalkyl, cycloalkenyl, cycloalkylalkyl, or cycloalkenylalkyl; C 2-8  alkenyl or alkynyl; benzyl; or said R 1  members substituted with halogen, amino, nitro, cyano, hydroxy, C 1-8  alkoxy, C 1-8  alkylthio, --C(═X)YR 8 , --C(═X)R 9 , YR 10 , or NR 11  R 12  ; R 12  is C 1-6  haloalkyl;   R 3  is C 1-6  alkyl, C 1-6  haloalkyl, CHO or CH 2  OH;   R 4  members are independently an R 1  member, C 1-8  thioalkyl, C 1-8  polyalkoxyalkyl, carbamyl, halogen, amino, nitro, cyano, hydroxy, C 6   2-12  aryl, aralkyl or alkaryl, --C(X)YR 13 , --C(X)R 14 , YR 15 , or NR 16  R 17  group; or two R 4  groups may be combined through a saturated and/or unsaturated carbon, or --(C═X)--, linkage to form a cyclic ring having up to 9 ring members which may be substituted with an R 1  member, halogen, amino, nitro, cyano, hydroxy, C 6-12  aryl, aralkyl, alkaryl, --C(═X)YR 13 , --C(═X)R 14 , YR 15  or NR 16  R 17  ;   X is O, S(O) m , NR 19  or CR 20  R 21  ;   Y is O, S(O) m  or NR 22  ; wherein at least one R 4  member is a non-halogen:   R 8-22  are hydrogen, C 1-8  alkyl, C 3-8  cycloalkyl, cycloalkenyl, cycloalkylalkyl, or cycloalkenylalkyl, C 2-8  alkenyl or alkynyl, benzyl, or said R 1  members substituted with halogen, amino, nitro, cyano, hydroxy, C 1-8  alkoxy, C 1-8  alkylthio, C 6-12  aryl, aralkyl, alkaryl, carboxyl, alkoxy-C 1-8  -alkyl, C 1-8  alkylamino, di-C 1-8  -alkylamino, C 1-8  alkoxy, or carbamyl;   m is 0-2 and   n is 1-5.   
     
     
       6. Compositions according to claim 5 wherein the compound of Formula I is as in formula II: ##STR18## and agriculturally-acceptable salts and hydrates thereof wherein R 1  is C 1-6  alkyl; R 2  is C 1-6  haloalkyl;   R 3  is C 1-6  alkyl, C 1-6  haloalkyl, CHO or CH 2  OH;   R 5  and R 6  are independently halogen; and   R 7  is an R 1  member, ##STR19##  YR 10 , or NR 11  R 12 .   
     
     
       7. Composition according to claim 6 where in Formula II R 1  is CH 3  ;   R 2  is CF 3  ;   R 3  is CH 3 , CH 2  F or CF 2  H;   R 5  is F;   R 6  is Cl; and   R 7  is ##STR20##   
     
     
       8. Composition according to claim 7 wherein said compounds is selected from the group consisting of 2-chloro-5-[1,4-dimethyl-5-(trifluoromethyl)-1H-pyrazol-3-yl ]-4-fluorobenzoic acid, 1-methylethyl ester;   2-chloro-5-[1,4-dimethyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-4-fluorobenzoic acid ethyl ester;   2-chloro-5-[4-difluoromethyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-4-fluorobenzoic acid, 1-methylethyl ester; and   2-chloro-4-fluoro-5-[4-(fluoromethyl )-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]benzoic acid, 1-methylethyl ester.   
     
     
       9. Method for combatting undesirable plants in crops comprising applying to the locus thereof a herbicidally-effective amount of a compound according to Formula I: ##STR21## and agriculturally acceptable salts and hydrates thereof wherein R 1  is independently C 1-8  alkyl; C 3-8  cycloalkyl, cycloalkenyl, cycloalkylalkyl, or cycloalkenylalkyl; C 2-8  alkenyl or alkynyl; benzyl; or said R 1  members substituted with halogen, amino, nitro, cyano, hydroxy, C 1-8  alkoxy, C 1-8  alkylthio, --C(═X)YR 8 , --C(═X)R 9 , YR 10 , or NR 11  R 12  ; R 2  is C 1-6  haloalkyl;   R 3  is C 1-6  alkyl, C 1-6  haloalkyl, CHO or CH 2  OH;   R 4  members are independently an R 1  member, C 1-8  thioalkyl, C 1-8  polyalkoxyalkyl, carbamyl, halogen, amino, nitro, cyano, hydroxy, C 6-12  aryl, aralkyl or alkaryl, --C(X)YR 13 , --C(X)R 14 , YR 15 , or NR 16  R 17  group; or two R 4  groups may be combined through a saturated and/or unsaturated carbon, or --(C═X)--, linkage to form a cyclic ring having up to 9 ring members which may be substituted with an R 1  member, halogen, amino, nitro, cyano, hydroxy, C 6-12  aryl, aralkyl, alkaryl, --C(═X)YR 13 , --C(═X)R 14 , YR 15  or NR 16  R 17  ;   X is O, S(O) m , NR 19  or CR 20  R 21  ;   Y is O, S(O) m  or NR 22  ; wherein at least one R 4  member is a non-halogen;   R 8-22  are hydrogen, C 1-8  alkyl, C 3-8  cycloalkyl, cycloalkenyl, cycloalkylalkyl, or cycloalkenyl alkyl, C 2-8  alkenyl or alkynyl, benzyl, or said R 1  members substituted with halogen, amino, nitro, cyano, hydroxy, C 1-8  alkoxy, C 1-8  alkylthio, C 6-12  aryl, aralkyl, alkaryl, carboxyl, alkoxy-C 1-8  -alkyl, C 1-8  alkylamino, di-C 1-8  -alkylamino, C 1-8  alkoxy, or carbamyl;   m is 0-2 and   n is 1-5.   
     
     
       10. Method according to claim 9 wherein the compounds of Formula I is compounds according to Formula II: ##STR22## and agriculturally-acceptable salts and hydrates thereof wherein R 1  is C 1-6  alkyl; R 2  is C 1-6  haloalkyl;   R 3  is C 1-6  alkyl, C 1-6  haloalkyl, CHO or CH 2  OH;   R 5  and R 6  are independently halogen; and   R 7  is an R 1  member, ##STR23##  YR 10 , or NR 11  R 12 .   
     
     
       11. Method according to claim 10 wherein in the compound, salt and hydrate of Formula II. R 1  is CH 3  ;   R 2  is CF 3  ;   R 3  is CH 3 , CH 2  F or CF 2  H;   R 5  is F;   R 6  is Cl; and   R 7  is ##STR24##   
     
     
       12. Method according to claim 11 wherein said compound is selected from the group consisting of 2-chloro-5-[1,4-dimethyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-4-fluorobenzoic acid, 1-methylethyl 5 ester;   2-chloro-5-[1,4-dimethyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-4-fluorobenzoic acid ethyl ester;   2-chloro-5-[4-difluoromethyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3yl]-4-fluorobenzoic acid, 1-methylethyl ester; and   2-chloro-4-fluoro-5-[4-(fluoromethyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]benzoic acid, 1-methylethyl ester.